Chiral 3,4-dibenzyloxy-5-hydroxymethyl-2-thiazolylpyrrolidines under Mitsunobu conditions afforded the corresponding R-protected pyrrolidines and 2-deoxy-piperidines in different ratios depending on the stereochemistry of the starting pyrrolidine and the nature of the acid R-OH. A mechanistic scheme is proposed involving the formation of an aziridinium ion as an intermediate.
Titolo: | Ring Enlargement of polyhydroxylated pyrrolidines to piperidines by Mitsunobu reaction: A fortuitous synthesis of 1-Deoxy-L-Allonojirimicina |
Autori di Ateneo: | |
Autori: | A. DONDONI; RICHICHI, BARBARA; A. MARRA; D. PERRONE |
Data di pubblicazione: | 2004 |
Rivista: | |
Volume: | 10 |
Pagina iniziale: | 1711 |
Pagina finale: | 1714 |
Abstract: | Chiral 3,4-dibenzyloxy-5-hydroxymethyl-2-thiazolylpyrrolidines under Mitsunobu conditions afforded the corresponding R-protected pyrrolidines and 2-deoxy-piperidines in different ratios depending on the stereochemistry of the starting pyrrolidine and the nature of the acid R-OH. A mechanistic scheme is proposed involving the formation of an aziridinium ion as an intermediate. |
Handle: | http://hdl.handle.net/2158/340334 |
Appare nelle tipologie: | 1a - Articolo su rivista |
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